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Cindy Crawford Told Us the Stories Behind Her Most Iconic Photos

Cindy Crawford—the original model-turned-mogul, whose career longevity and brilliant business sensibilities are nothing short of awe-inspiring—is doing something she never thought she’d do: publishing a book, Becoming, to coincide with her upcoming 50th birthday. But this isn’t the typical, glossy, fancy coffee table book that you’d expect from an iconic beauty who’s shot with everyone from Herb Ritts to Steven Meisel and has hundreds of covers under her belt. “I’ve done a lot of incredible pictures, but I don’t see my career that way,” Crawford says. While the book does include a slew of phenomenal, handpicked photos documenting Crawford’s illustrious career, she’s also written a series of essays telling the story of how she went from a small town girl to the world’s biggest supermodel to a powerhouse businesswoman. (In addition to numerous other successful ventures over the years, Crawford is currently at the helm of two major brands, Cindy Crawford Home and the skincare line Meaningful Beautiful.) Expanding her portfolio far beyond that which made her first famous, Crawford helped pave the way for future celebrity entrepreneurs like Gwyneth Paltrow, Reese Witherspoon, and Blake Lively.

In an exclusive interview with Byrdie, Crawford looks back on some of her most iconic photos, sharing never-before-heard stories behind the beauty and fashion looks for each image. Keep scrolling!

Byrdie: Congratulations on Becoming! Why did you want to do this book? Cindy Crawford: Two years ago I was with my publicist Annett [Wolf] and this other woman who has worked with me for like 15 years, and we were talking about how I was getting ready to turn 48, knowing 50 was on the horizon, and just over that lunch I thought, well maybe [the book] could be 50 iconic images with 50 essays about the lessons to celebrate turning 50. I went with Rizzoli, but they thought a 100-page book was going to feel very thin, very flimsy, so once we threw away the constructs of 50, 50, then we were able to include a lot more images, which is fun and more freeing.

B: What is your favourite cover or shoot of all time? CC: I think my favorite shoot of all time was a shoot I did with Herb Ritts for Rolling Stone, where I was playing different characters, and the hair and makeup people were so incredible. I mean Peter Savic, he just does wigs like nobody’s business, but Francesca Tolot did the makeup, and what she was really good at was transforming me within 15 minutes, knowing what was important to do and also what really didn’t matter. It gave me enough to be able to get into character.

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Justin Coit

Credit: Maje coat.

B: Have you given any beauty or career advice to your daughter?CC: I’m in charge of tweezing her eyebrows, because I don’t want her to over-tweeze. Fortunately, she listens to me about stuff. But really, she has access to YouTube and she can do her own makeup great already. I tell her as a model, your job is to go and not be a diva. If they ask you your opinion, you can give it, but if they don’t, you just do [what they ask] and make it look as good as you can. Same with the clothes: it’s your job to make them look good, it’s not your job to love them. When she went to go work with Bruce Weber, and my son as well, [I said] do your homework, look at Bruce Weber’s pictures so you understand his language. Then she got to shoot with Steven Meisel, and again, look at Steven, he likes a different kind of body language. I think for all young models, if you’re going to work with a photographer, it’s important to look at their work and understand how you can be a better model for them.

B: Contouring had a big moment in the late '80s and early '90s: How do you feel about it being “back” in such a big way?CC: Look, that’s fashion, right? I thought I could never go back to high-waisted jeans, but all of a sudden they felt right again. But some things that look good in pictures can look too heavy in real life, and that would be my only caution. I wouldn’t want anyone to ever say to me or my daughter, “Wow, your makeup looks amazing.” [You want them to think] you look amazing.

B: Who are some of your go-to beauty gurus?CC: Sonia Kashuk has been my friend for such a long time and she’s a makeup artist and a woman and she’ll tell it to me straight. And I like that about her and I like her products and I love her message, which is that makeup is just a tool to enhance a woman’s natural beauty; it’s not about total transformation. And Miles Haddad, he colours my hair. It’s really hard to get brunette hair in L.A, because they think that secretly you want to be a blonde. So after two months, all of a sudden it’s like: “Oh my God, I’m blonde,” and you have to go back. So he’s been really good at helping me maintain an L.A. brunette, which is different from a New York brunette, because L.A. brunette, you have been in the sun and it can’t look like a solid colour, whereas in New York in the winter a solid colour looks really rich and appropriate.

B: What products do you carry with you reguarly?CC: I usually have La Mer's Crème de la Mer ($225) just for hydration and then I usually have a Sonia Kashuk lip gloss if I’m going to a meeting and need a little colour.

B: What's your most recent beauty discovery? CC: It’s a device. I think devices are really cool. Last week I was doing a commercial and I needed to be on set every day at 6 a.m. I always say I can get up at whatever time you want, but my face, I’m not sure what time it’s going to wake up. And I find when I use the [Foreo Luna Mini] and I put on my cleanser, before I even take a shower, it just brings the blood supply to my skin and you know if you have pillow marks or whatever, it just helps everything settle faster in the morning.

B: You’ve said sleep is super important: Do you have any tricks for winding down/staying asleep?CC: I try to go to bed between 10 p.m. and 11 p.m. every night. I exercise and don’t drink coffee. I get up early, so I don’t have a problem going to sleep. Sometimes I have a problem staying asleep if I have too much on my mind. But if it’s after 4 [a.m.] and I wake up, I just get up because I can get so much done when it’s quiet.

B: Can you tell us about joining Taylor Swift's "Bad Blood" video?CC: When she reached out to me, they were already done shooting, but they saved this little spot that they thought I would be right for. For me, there was such an incredible message in that video that I was happy to be a part of it. Kaia thought I was so cool, because I was in the same video as Gigi Hadid. It made me cool to my own kids, so thank you Taylor.

Now for the fun part! We'd love for you to share the stories behind some of your most iconic looks.

“I write about this in the book, how it just was the right combination of the right shorts, the right music [Ed note: the song was “Just One Look” by Doris Troy], and it was just very Americana with the little boys. It was sexy, but there was a sweetness to it, too. I think those might have been my jeans that we cut off at the shoot, and then it’s funny because I did a remake of that commercial after I had kids and I wore the same shorts, but we had to take the waist down, because then it was more high-waisted and so we had them remade. But it was just everything: the car, the music…Peter Savic did the hair, and it was just big and sexy, and back then it was like the hair couldn’t be too big. We didn’t use extensions though; extensions are relatively new. That was all backcombing, so it was a lot harder on your hair to get the look.”

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Rose Hartman/WireImage

“I have no explanation on the hair. The dress was obviously a Versace bondage dress—love. I think that we decided if I had my hair down you wouldn’t see all of the bondage stuff on the top, so it’s a little bit Pebbles. The makeup actually looks like Kevin Aucoin; I don’t remember who did it, but it definitely has that nobody-thinks-you’re-not-wearing-makeup look. You know, the expression is practically painted on your face. And then that’s an extension, because I don’t think my hair was that long.”

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Michel Comte for Vogue Italia

“The photographer was Michel Comte, and I know we shot it in Los Angeles and Rita Hayworth was the inspiration. I think Carol Shaw did the makeup. I’ve done pictures where you’re literally doing Marilyn [Monroe] or it’s like a modern version of it, and I felt like this was a modern version of Rita, and how we saw her—definitely like Gilda. I think as a model, when you have an inspiration like that, it makes it…you really feel like you’re playing a part and it gives you an attitude, like when you’re doing Marilyn and Rita, and you can channel what you think that is.”

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Rocco Laspata for Capezio

“That photographer is Rocco Laspata. They [Ed note: meaning Capezio] almost wanted [the photos] to feel like film stills, and so I don’t know if this was Gina Lollobrigida or Raquel Welch or Sophia Loren, but we were in Capri. They don’t just ask you to imagine it, they put you in the environment and then you channel that. But to me, what I see is Oribe, when he gave me the blonde chunk. It’s funny, because so many of my friends who are hairdressers were like, “Do you know how many women asked for that chunk?” And the interesting thing about the chunk is that it didn’t look good in real life, it was too contrast-y, but it photographed really cool, because you got that little more extreme than a highlight. We were selling shoes, but I don’t even see a shoe or a bag in sight, so it was more about creating a brand identity, really, a fantasy for women to feel like: Oh, if I wear that bag I will feel like I’m in Capri.”

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Antoine Verglas for ELLE

“This is an oldie. I like it, just because even today we shot that white shirt, and I think there’s something about men’s pajamas or a men’s shirt that is sexy in an innocent way. There wasn’t much of a hair and makeup story. I think that’s the balance of a real girl.”

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Jim Smeal/WireImage

“That was my first time going to the Oscars and I had just done the shows in Milan. I had done Versace, and that dress was in the show in black, and I loved it, so they made it for me in red. It was a bit scandalous at the time, not even the front, but the back. It was slit up to my bum. People always dressed up for the Oscars, but it wasn’t such a fashion show that it is now. But I was like, I’m a model, I’m not an actress, so I better have a rockin’ dress on.”

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Peter Lindbergh for British Vogue

“I wrote about this in the book. Herb [Ritts] shot all of us—except Tatjana [Patitz] wasn’t in that, but Stephanie Seymour was—he shot us all together for Rolling Stone, but it hadn’t come out yet. And then Liz Tilberis from British Vogue, asked [Peter Lindberg] to shoot who was the going to be the face of the ‘90s, and he didn’t think it could be just one face, it had to be different faces, which was cool, and so he assembled us to do this. And it was Giorgio di Sant’ Angelo bodysuits, but with jeans, very kind of approachable and American, and not a lot of hair and makeup. It was really about…maybe that’s what made it unique too, was that it was about the women. That it’s not about the hair, it’s about the lack of hair or the lack of makeup, and even about the lack of styling, really. We look like real women there, all individual and unique. And then from that cover, George Michael decided that he did not want to not be in his own video [Ed note: referring to the “Freedom! 90” video] and that he wanted all of us in it. And David Fincher was shooting it, so how can you say no? I think even what Fincher did with the video was to continue that theme that we are each different. He didn’t try to have us coming out together looking all the same, but celebrated kind of what he thought was sexy about each one of us. The song was a great song and the video cemented it in time. And then culminating with the Versace show at the end of it, walking down the runway with everyone except Tatjana to that song, it was like wait, something is happening here. To me, I would say that was my biggest supermodel moment. I felt like a rock star when we were on stage.”

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Robin Platzer/Images/Getty Images

“To me this is very Revlon. Revlon always liked their girls to wear red. The hair is very Rita Hayworth. It’s funny, when I look at this now I think: Oh I was so young, why was I trying to dress so [grown up]—I should have been dressing younger. I was probably in my early twenties there and you think, “I’m going to a glamorous event, I need to put on my lady look.” Actually, that dress looks like it was Giorgio di Sant’ Angelo. To me, [the look] seems very of the time."

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Arthur Elgort for Vogue Italia

“That was shot at a dude ranch, where my sister was working, and Arthur [Elgort] and Sonia [Kashuk] the makeup artist, who is one of my best friends, she knew that my sister was working at this dude ranch so she said to Arthur, “Let’s do a story at this ranch.” And I love that makeup; it’s super edgy. And in the story there were three beauty [looks]. There was this one, and then there’s one where my hair is really big and frizzy without the dark eyes, and then there’s one where I’m wearing a cowboy hat and sunglasses. So within the story it was really interesting, because there were a lot of different looks, and I think that’s really fun for the hair and makeup people to get to play like that. That was just like cool-chic, right?”

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Steven Meisel for Lei Italia

“That was for Le Italia—that was crazy! I love the makeup, though. I think that’s very classic, it’s almost like those old American Vogue covers, you know where it was [cropped] from the bust up, sideways, and with the head turn. It’s all about the eyebrow, but that hair is crazy—and the earrings! Kevin Aucoin did the makeup, and if I had to guess, I would say Oribe did the hair, possibly.”

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Wayne Maser for Vogue

“This was the first time I shot for American Vogue. It was in St. Bart’s and Carlyne Cerf [de Dudzeele] was the stylist and Wayne Maser was shooting. Because of this shoot, I got my cover try with Richard Avedon for my first Vogue cover, but it was hard because I was completely sunburned. We were shooting out in full-on sun all day long, and I was so young and wanting to please, I didn’t say, “Excuse me, I’m getting sunburned.” From the second day, you could see in one of the pictures I’m literally the colour of a lobster. But actually my hair, before this happened I was doing a shoot for Italian Vogue with Patrick Demarchelier and [the hair stylist] cut my ponytail off without asking. I was crying. And this was just when I left Chicago and my hair was still growing out and it was kind of a weird length, but it looked super modern.”